Transannular Strain
Perhaps surprisingly, medium sized rings (between 7-13 carbons) experience more strain energy than cyclohexane. This transannular strain occurs when the cycloalkanes attempt to avoid angle and torsional strain. In doing so, CH2 units across from each other are brought into proximity and experience Van der Waals strain.
Read more about this topic: Strain (chemistry), Kinds of Strain, Ring Strain
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